Asymmetric Total Synthesis of (+)-Nominine: Development of a Dual Cycloaddition Strategy for the Synthesis of the Hetisine Alkaloids
Peese, Kevin M.
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https://hdl.handle.net/2142/84279
Description
Title
Asymmetric Total Synthesis of (+)-Nominine: Development of a Dual Cycloaddition Strategy for the Synthesis of the Hetisine Alkaloids
Author(s)
Peese, Kevin M.
Issue Date
2007
Doctoral Committee Chair(s)
Gin, David Y.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
A dual cycloaddition strategy for the synthesis of the hetisine alkaloids has been developed and applied to the asymmetric total synthesis of nominine. The approach relies on an early stage intramolecular aza-1,3-dipolar cycloaddition of a 4-oxidoisoquinolinium betaine with an ene-nitrile dipolarophile and a late stage intramolecular [4+2] Diels-Alder cycloaddition. Also of note is the development of a new method for the preparation of 4-oxidoisoquinolinium betaines. Overall, a 16 step asymmetric synthesis of (+)-nominine was accomplished in 1.3% yield, while (+/-)-nominine was prepared in 15 steps in 6.1% yield.
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